Assignment | 12C-Mass [M + H]+ (m/z) | Proposed Structure | Important MS Fragments (m/z) | 1H-NMR (δ) |
---|---|---|---|---|
Rivaroxaban | 436 | 231, 145 | 7.59 (ps-d, 2H), 7.51 (d, 1H), 7.37 (ps-d, 2H), 7.05 (d, 1H), 7.18 (d, 1H), 4.89 (m, 1H), 4.27 (s, 2H), 4.20 (t, 1H), 4.03 (ps-t, 2H), 3.90 (dd, 1H), 3.73 (ps-t, 2H), 3.72 (d, 2H) | |
M-1 | 468 | 424, 406, 396, 362, 262, 219, 145 | 7.53 (ps-d, 2H), 7.52 (d, 1H), 7.40 (ps-d, 2H), 7.06 (d, 1H), 4.88 (m, 1H), 4.22 (t, 1H), 3.9 (overlapping with residual solvent signal, 1H), 3.78 (t, 2H), 3.64 (t, 2H), 3.74 (dd, 1H), 3.68 (dd, 1H) | |
M-2 | 452 | 406, 362, 145 | 7.58 (ps-d, 2H), 7.51 (d, 1H), 7.37 (ps-d, 2H), 7.05 (d, 1H), 5.27 (s, 1H), 4.90 (m, 1H), 4.36 (m, 2H), 4.21 equatorial (t, 1H), 3.9 (overlapping with residual solvent signal, 3H), 3.72 (d, 2H), 3.56 (m, 2H) | |
M-3 | 452 | 434, 406, 145 | 7.59 (ps-d, 2H), 7.52 (d, 1H), 7.34 (ps-d, 2H), 7.05 (d, 2H), 5.09 (ps-quart, 1H), 4.90 (m, 1H), 4.35 (d, 1H), 4.24 (d, 1H), 4.22 (t, 1H), 4.04 (dd, 1H), 3.9 (overlapping with residual solvent signal, 2H), 3.72 (d/overlapping with residual solvent signal, 2H) | |
M-4 | 220 | 202, 174, 145 | 7.56 (d, 1H), 7.06 (d, 1H), 3.81 (s, 2H) | |
M-5 | 454 | 396, 292, 191, 145 | 7.60 (ps-d, 2H), 7.51 (d, 1H), 7.33 (ps-d, 2H), 7.05 (d, 1H), 4.90 (m, 1H), 4.21 (t, 2H), 4.19 (overlapping with residual solvent signal, 2H), 3.9 (overlapping with residual solvent signal, 2H), 3.78 (m/overlapping with residual solvent signal, 2H), 3.72 (m/overlapping with residual solvent signal, 2H), 3.59 (m/overlapping with residual solvent signal, 2H) | |
M-6 | 396 | 191, 145 | 7.52 (d, 1H), 7.22 (ps-d, 2H), 7.05 (d, 1H), 6.70 (ps-d, 2H), 4.84 (m, 1H), 4.10 (t, 1H), 3.79 (m/overlapping with residual solvent signal, 1H), 3.69 (m, 2H), 3.67 (t, 2H), 3.19 (t, 2H) | |
M-7 | 454 | 408, 378, 145 | 7.53 (d, 1H), 7.23 (ps-d, 2H), 7.06 (d, 1H), 6.74 (ps-d, 2H), 4.85 (m, 1H), 4.11 (equatorial)—3.79 (axial) (t and dd, 2H), 3.85 (s, 2H), 3.69 (d, 2H), 3.65 (t, 2H), 3.23 (t, 2H) | |
M-8 | 452 | 434, 406, 145 | Chemical shifts are similar to those of rivaroxaban except for the protons on the morpholinone moiety: 5.41 (t, 1H), 4.40 (d, 1H), 4.26 (d, 1H), 3.87 (overlapping with residual solvent signal, 1H), 3.56 (overlapping with residual solvent signal, 1H) | |
M-9 | 452 | 434, 273, 261, 145 | Chemical shifts are similar to those of rivaroxaban except for the protons on the oxazolidinone moiety: 5.71 (d, 2H), 4.56 (d/t, 1H), 3.79 (dd, 1H), 3.68 (dd, 1H) | |
M-10 | 468 | 422, 404, 289, 277 | No data available | |
M-11 | 468 | 422, 352, 278, 145 | No data available | |
M-12 | 408 | 247, 216, 193, 145 | No data available | |
M-13 | 161 [M — H]- (ESI negative) | No MS/MS spectra in positive ionization mode, only detectable in ESI negative | No data available | |
M-14 (CTCA) | 162 | No data available | ||
M-15 (S)-oxamine | 292 | 231, 205, 193 | No data available | |
M-16 | 291 | |||
M-16 (hydrate) | 309 | 291, 205 | (hydrate in DMSO-d6): 7.58 (d, 2H); 7.38 (d, 2H); 5.4 (bs, ca, 2H); 4.95 (s, 1H); 4.45 (m, 1H); 4.19 (s, 2H); 3.78-4.08 (m, 4H); 3.70 (m, 2H) | |
M-17 | 293 | 237, 205, 193 | (in DMSO-d6): 7.58 (d, 2H); 7.42 (d, 2H); 5.21 (m, 1H); 4.70 (m, 1H); 4.19 (s, 2H); 4.08 (t, 1H); 3.98 (m, 2H); 3.85 (t, 1H); 3.62-3.78 (m, 3H); 3.58 (m, 1H) | |
M-18 | 307 |
| 261, 248, 235 | (sodium salt in DMSO-d6): 7.57 (d, 2H); 7.38 (d, 2H); 4.64 (m, 1H); 4.18 (m, 3H); 3.87-3.95 (m, 3H); 3.70 (t, 1H) |
CTCA, 5-chlorothiophene-2-carboxamide; ESI, electron spray ionization; MS/MS, tandem mass spectrometry.